Barry Strauss, a classicist and military historian, shares insights on the Roman Caesars and their leadership lessons. He discusses how Augustus consolidated power and contrasts him with the notorious Nero, whose urban renewal efforts challenge the 'bad emperor' narrative. Strauss highlights Vespasian's innovative rise and Marcus Aurelius’s struggles, revealing how philosophical ideals often clash with the harsh realities of governance. The conversation uncovers timeless strategies that shaped the Roman Empire and continue to resonate in modern leadership.